The Roommate

[Fiction]

I moved in with Nina about three months ago. She needed a roommate and I responded to her post on Craigslist. We met on her front porch and my first thought about her was, "oh my god, she's gorgeous." Nina was brunette with a slender build and athletic body. She was barefoot, wearing leggings and a cropped sweatshirt like she was about to head to the gym when we were finished.

I took a quick tour of her small, two-bedroom, two-bathroom house, it was very clean with nice modern touches and brand new appliances. Her room and mine were next to each other but had opposite floor plans. There was a tint of color overtaking her bedroom as she muted some of the sunlight with a Transgender Pride flag. After the tour we chatted in the living room for about a half-hour before she offered me the open room. I excitedly agreed and signed the lease on the spot.

After a long weekend moving everything in, she threw a housewarming party and had me invite some friends. It wasn't anything crazy, just a little drinking and some fun games. A few times I caught the eye of Nina's friend Jade, another gorgeous transgender woman with caramel skin and jet black hair who lived a block away. We played on the same team for one of the games and got a little touchy and flirty before the night was over. Before she left, she whispered something into Nina's ear and they both looked at me and giggled.

A few weeks later I was home by myself on a Thursday with the day off. It was the middle of the day and Nina would be at work for a few more hours. I finally had the courage to snoop around her bedroom a little bit and get to know the girl I was living with. I'd peeked around the door a couple times but today I was going in.

I started with the bedside table and opened a drawer filled with sex toys, vibrators, dildos and a fleshlight that were all neatly organized. I opened up some dresser drawers as well, one had t-shirts, one had jeans and sweatshirts, another had bras and all sorts of panties. The bottom drawer was filled with leggings and pantyhose. I had a little experience crossdressing on my own but not with a selection anywhere near what was in front of me. The urge to do it again came over me so hard that the next thing I knew, I was naked and slipping on a black lace thong and bra. I grabbed a pair of black leggings from the drawer and pulled over the same cropped sweatshirt Nina was wearing when we met.

Finally I got to the closet, I slid the door open to see a giant rack of shoes of all kinds and dresses and blouses of all colors stuffed into the closet on countless hangers. I wanted to touch everything. One pair of shoes stuck out to me, bright white platform sneakers. I'd always secretly liked checking out the girls who wore them and the prospect of trying them on myself excited me so much that it became much more difficult to hide my erection in Nina's thong. I slipped them on and they fit perfectly. I noticed a few wigs on the top shelf of the closet so I slowly took down the nearest one, a brunette bob cut, and carefully put it over my head.

I left Nina's room to check myself out in the full-length mirror she left out in the living room. My ass looked surprisingly great and almost unrecognizable in her leggings. I loved the way I looked and was about to head to her bathroom to try on some makeup when the front door opened. It was Nina.

"What the hell are you doing?? Why are you in my clothes??"

"I...uh..." I was stammering. She shut the door behind her and took a step toward me. I sighed and looked down at the floor.

"You could have just told me you liked crossdressing!" she said in a cheery voice.

I was shocked. I looked up at her with a puzzled face.

"Oh, uh...yeah....I guess I do...it's uh..."

"Say no more," she said. "Trust me, I know exactly how you feel." She motioned to the pride flag hanging in her room.

"It's not really like that..." I said.

"Oh I know," she replied with a wry smile, holding up one finger as she took out her phone with her other hand to make a call.

"Hey..." she said into the phone. "You were right! ....Yep, good call....We're going to have some fun, come on over...K, see you soon, muah!"

Now I was even more confused, "What was that??"

"Oh that was Jade, my friend from down the street. You seemed quite interested in her at the party. Remember afterwards how you saw us whispering and giggling about you? She predicted this would happen and now she gets to come over and play."

Before I knew it, there was a knock at the door.

"And there she is!"

I was terrified what Jade would think of me dressed in Nina's clothes but before I could even process the thought, she burst in the door wearing nearly the exact same outfit I was.

"OMG twinsies!!" She said and gave me a big hug. I was stunned but hugged her back. "Let's get some makeup on you, I want my cutie all dolled up for playtime."

Jade took my hand and led me into Nina's bathroom. I looked back at Nina who blew me a kiss.

"I'll be right in!" Nina said as she walked into her bedroom.

Jade worked as a makeup artist and assured me that I was in good hands, "I'm going to make you look sooooo pretty! And not like a drag queen, like a real girl."

After about 15 minutes, and all sorts of brushes and colors, she held up a mirror to my newly painted face. I could barely recognize myself. Perfect contouring, rosy red cheeks, glittery eyes with dark mascara and bright red lipstick.

Nina appeared in the doorway, "I thought I'd join the party." She was wearing the same thing as Jade and me and she looked amazing.

"Somebody is getting a little excited" Jade said and pointed down at my crotch. I had gotten so hard that it was clearly showing through the leggings.

"And somebody clearly didn't learn to tuck either." Nina said. "I'll show you what a quality tuck looks like."

She slipped her leggings down to reveal a pink thong. When that came down, it revealed a well-tucked, soft cock. My eyes got wide and mouth dropped open just a bit.

"Ohhh, looks like someone wants a taste? Come here sweetheart, pretty girls love cock."

I slowly nodded. Nina stepped forward and l kissed her tip, then licked underneath and in a fit of horny angst, took the entire thing into my mouth. It was my first time and it felt so, so good. I slurped over her, my tongue swirling around her shaft, in and out until I felt her getting hard in my mouth.

"I want a turn!" Jade said and stood next to Nina. By now I was on my knees looking up at two gorgeous transgender women, feeling more feminine that I had in my entire life. My ultimate fantasy was becoming reality. Jade took her leggings and thong down at the same time, almost forcing Nina out of my mouth with her cock.

I sucked on her head like a lollipop and felt Nina grab my hips.

"You got me all lubed up and I need somewhere to go!" She started peeling the leggings off of me and smacked my bare ass. She rubbed on some lube and teased my hole with her tip before slowly pushing forward. I felt her pop in but was too busy thinking about sucking on Jade to feel any pain and in just seconds, Nina was all the way inside me with her tummy against my ass.

I let out a deep, long moan, muffled by Jade's piece filling my mouth.

"Such a good girl!" Jade said, pulling out of my mouth so she could kiss me as Nina started thrusting. After a quick make out, her cock was back in my mouth. It was euphoric. Nina's hands around my waist, Jade's on my shoulders and mine on the ground, barely able to hold myself up from all of the stimulation.

Suddenly, Nina slid her right hand inward and wrapped it around my cock, slowly stroking me in rhythm with her thrusting. I let out another deep, muffled moan then wrapped my lips around Jade again and sucked her like a popsicle. I could taste her precum leaking out and she started to squirm and moan. She tensed up, let out a bit squeal and a spurt of hot cum hit the back of my throat. Then another, and another, and more until eventually she stopped squealing and pulled out of my mouth.

I licked her clean as she said, "Now it's my turn!"

Jade crawled under me and sealed her lips over my cock, teasing me with her tongue. Nina kept pushing until I heard her squeal. She tightened her grip on me and pumped hard for five seconds. It was unlike anything I had felt before and the moment I felt her come inside me, I burst into Jade's mouth.

We all laid on the bed, spent for what felt like ten minutes before we all started giggling.

"Wow, that was incredible." I said.

"Time to clean yourself up," said Nina. "We're taking you to the mall so you don't have to steal my clothes again."

"Oooh, I want to pick out an outfit for her!" Jade said with a smile. "Something easily accessible so I can be the one that fucks her next time."

Jade leaned in and kissed me, probably for a little bit too long because Nina smacked my ass and told us to get a room.

I looked in the mirror again to fix my hair before we left, loving what I saw and excited for what was to come next.